首页|Indole alkaloid glycosides with a 1'-(phenyl)ethyl unit from Isatis indigotica leaves

Indole alkaloid glycosides with a 1'-(phenyl)ethyl unit from Isatis indigotica leaves

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Seven indole alkaloid glycosides containing a 1'-(4"-hydroxy-3",5"-dimethoxyphenyl)ethyl unit (1-7) were isolated from an aqueous extract of Isatis indigotica leaves (da qing ye).Their structures were determined by spectroscopic data analysis combined with enzymatic hydrolysis as well as comparison of their experimental CD (circular dichroism) and calculated ECD (electrostatic circular dichroism) spectra.Based on analysis of[α]D20 and/or Cotton effect (CE) data of 1-7,two simple roles to assign location and/or configuration of β-glycopyranosyloxy and 1'-(phenyl)ethyl units in the indole alkaloid glycosides are proposed.Stereoselectivity in plausible biosynthetic pathways of 1-7 is discussed.Compounds 3 and 4 and their mixture in a 3∶2 ratio showed activity against KCNQ2 in CHO cells.The mixture of 5 and 6 (3:2) exhibited antiviral activity against influenza virus H1N1 PR8 with IC50 64.7 μmol/L (ribavirin,IC5o 54.3 μmol/L),however,the individual 5 or 6 was inactive.Preliminary structure-activity relationships were observed.

CruciferaeIsatis indigoticaIndole alkaloid glycosideIsatidifoliumosidesEpiisatidifoliumosidesKCNQ2 inhibitionAnti-influenzaAnti-virusActivity

Qinglan Guo、Dawei Li、Chengbo Xu、Chenggen Zhu、Ying Guo、Haibo Yu、Xiaoliang Wang、Jiangong Shi

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State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica,Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

Financial support of the National Natural Science Foundation of ChinaFinancial support of the National Natural Science Foundation of ChinaFinancial support of the National Natural Science Foundation of ChinaFinancial support of the National Natural Science Foundation of ChinaCAMS Innovation Fund for Medical Science of ChinaCAMS Innovation Fund for Medical Science of Chinaand the Drug Innovation Major Projectand the Drug Innovation Major Project

8163009421732008817300932017-I2M-3-0102016-I2M-1-0102018ZX09711001-001-001Chin

2020

药学学报(英文版)

药学学报(英文版)

CSTPCDCSCDSCI
ISSN：
年,卷(期)：2020.10(5)
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